Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199013827/sk1338sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199013827/sk1338Isup2.hkl |
CCDC reference: 142728
The title complex was prepared by the reaction of imidazole (1 g, 15 mmol) with Ni(p—CH3O·C6H4COO)2·4H2O (Ephraim & Pfister, 1925) (1 g, 2.5 mmol) in warm ethanol (50 ml). Single crystals suitable for X-ray analysis were obtained by recrystallization from ethanol.
After checking their presence in the difference map, all H-atoms were geometrically fixed and allowed to ride on their attached atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
Fig. 1. The molecule structure of the title complex. Displacement ellipsoids are shown at the 30% probability level. H atoms are omitted for clarity. | |
Fig. 2. Part of the three-dimensional network. |
[Ni(C3H4N2)6](C8H7O3)2 | Z = 1 |
Mr = 769.48 | F(000) = 402 |
Triclinic, P1 | Dx = 1.377 Mg m−3 |
a = 9.8185 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5191 (4) Å | Cell parameters from 5621 reflections |
c = 10.8556 (5) Å | θ = 2.7–61.1° |
α = 61.474 (1)° | µ = 0.58 mm−1 |
β = 76.764 (1)° | T = 293 K |
γ = 70.973 (1)° | Parallelopiped, pale blue |
V = 927.62 (7) Å3 | 0.50 × 0.24 × 0.14 mm |
Siemens SMART CCD area detector diffractometer | 4138 independent reflections |
Radiation source: fine-focus sealed tube | 3474 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.7° |
ω scans | h = −12→12 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −13→12 |
Tmin = 0.759, Tmax = 0.923 | l = −14→14 |
6314 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3 |
4140 reflections | (Δ/σ)max < 0.001 |
241 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −1.05 e Å−3 |
[Ni(C3H4N2)6](C8H7O3)2 | γ = 70.973 (1)° |
Mr = 769.48 | V = 927.62 (7) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.8185 (4) Å | Mo Kα radiation |
b = 10.5191 (4) Å | µ = 0.58 mm−1 |
c = 10.8556 (5) Å | T = 293 K |
α = 61.474 (1)° | 0.50 × 0.24 × 0.14 mm |
β = 76.764 (1)° |
Siemens SMART CCD area detector diffractometer | 4138 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3474 reflections with I > 2σ(I) |
Tmin = 0.759, Tmax = 0.923 | Rint = 0.039 |
6314 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.74 e Å−3 |
4140 reflections | Δρmin = −1.05 e Å−3 |
241 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −35°. Coverage of the unique set is over 97% complete. Crystal decay was monitored by repeating thirty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. The structure was solved by direct methods and refined by full-matrix. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 1.0000 | 0.0000 | 0.0000 | 0.02620 (14) | |
O1 | 0.7181 (2) | 0.5723 (2) | 0.37875 (19) | 0.0516 (5) | |
O2 | 0.4355 (2) | 0.11618 (19) | 0.35781 (16) | 0.0413 (4) | |
O3 | 0.4316 (2) | 0.28877 (18) | 0.13656 (16) | 0.0407 (4) | |
N1 | 0.9064 (2) | −0.0372 (2) | 0.20911 (19) | 0.0340 (4) | |
N2 | 0.7497 (3) | −0.0666 (3) | 0.3960 (2) | 0.0458 (5) | |
H2A | 0.6694 | −0.0718 | 0.4482 | 0.055* | |
N3 | 1.0730 (2) | −0.2351 (2) | 0.0674 (2) | 0.0330 (4) | |
N4 | 1.1969 (3) | −0.4591 (2) | 0.0882 (3) | 0.0473 (5) | |
H4A | 1.2612 | −0.5281 | 0.0706 | 0.057* | |
N5 | 1.1954 (2) | 0.0005 (2) | 0.0552 (2) | 0.0321 (4) | |
N6 | 1.3347 (2) | 0.0761 (3) | 0.1252 (2) | 0.0448 (5) | |
H6A | 1.3674 | 0.1341 | 0.1395 | 0.054* | |
C1 | 0.7706 (3) | −0.0366 (3) | 0.2592 (3) | 0.0386 (5) | |
H1A | 0.6981 | −0.0177 | 0.2061 | 0.046* | |
C2 | 0.8783 (4) | −0.0871 (4) | 0.4362 (3) | 0.0572 (8) | |
H2B | 0.8971 | −0.1089 | 0.5253 | 0.069* | |
C3 | 0.9751 (3) | −0.0696 (4) | 0.3213 (3) | 0.0503 (7) | |
H3A | 1.0729 | −0.0784 | 0.3190 | 0.060* | |
C4 | 1.0162 (3) | −0.3416 (3) | 0.1835 (3) | 0.0499 (7) | |
H4B | 0.9371 | −0.3219 | 0.2437 | 0.060* | |
C5 | 1.0932 (4) | −0.4790 (3) | 0.1967 (3) | 0.0583 (8) | |
H5A | 1.0776 | −0.5700 | 0.2669 | 0.070* | |
C6 | 1.1806 (3) | −0.3111 (3) | 0.0132 (3) | 0.0422 (6) | |
H6B | 1.2389 | −0.2675 | −0.0677 | 0.051* | |
C7 | 1.3081 (3) | −0.1177 (3) | 0.1186 (3) | 0.0411 (6) | |
H7A | 1.3236 | −0.2143 | 0.1289 | 0.049* | |
C8 | 1.3936 (3) | −0.0727 (3) | 0.1639 (3) | 0.0459 (6) | |
H8A | 1.4759 | −0.1317 | 0.2117 | 0.055* | |
C9 | 1.2171 (3) | 0.1152 (3) | 0.0613 (3) | 0.0418 (6) | |
H9A | 1.1572 | 0.2115 | 0.0251 | 0.050* | |
C10 | 0.6589 (3) | 0.4831 (3) | 0.3587 (2) | 0.0363 (5) | |
C11 | 0.6449 (3) | 0.3424 (3) | 0.4589 (2) | 0.0410 (6) | |
H11A | 0.6789 | 0.3009 | 0.5467 | 0.049* | |
C12 | 0.5797 (3) | 0.2634 (3) | 0.4272 (2) | 0.0363 (5) | |
H12A | 0.5693 | 0.1695 | 0.4950 | 0.044* | |
C13 | 0.5302 (2) | 0.3222 (2) | 0.2964 (2) | 0.0288 (4) | |
C14 | 0.5459 (3) | 0.4635 (3) | 0.1963 (2) | 0.0342 (5) | |
H14A | 0.5136 | 0.5042 | 0.1079 | 0.041* | |
C15 | 0.6089 (3) | 0.5440 (3) | 0.2267 (2) | 0.0378 (5) | |
H15A | 0.6179 | 0.6385 | 0.1593 | 0.045* | |
C16 | 0.7736 (4) | 0.5142 (4) | 0.5106 (3) | 0.0561 (8) | |
H16A | 0.8117 | 0.5870 | 0.5115 | 0.084* | |
H16B | 0.8491 | 0.4245 | 0.5245 | 0.084* | |
H16C | 0.6974 | 0.4919 | 0.5848 | 0.084* | |
C17 | 0.4598 (2) | 0.2357 (2) | 0.2626 (2) | 0.0289 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0262 (2) | 0.0272 (2) | 0.0262 (2) | −0.00938 (15) | 0.00287 (14) | −0.01298 (17) |
O1 | 0.0689 (13) | 0.0571 (12) | 0.0438 (10) | −0.0382 (11) | 0.0003 (9) | −0.0219 (10) |
O2 | 0.0572 (11) | 0.0391 (9) | 0.0270 (8) | −0.0267 (9) | 0.0030 (7) | −0.0078 (7) |
O3 | 0.0645 (12) | 0.0300 (8) | 0.0280 (8) | −0.0128 (8) | −0.0131 (8) | −0.0086 (7) |
N1 | 0.0356 (10) | 0.0363 (10) | 0.0303 (9) | −0.0111 (8) | 0.0053 (8) | −0.0169 (9) |
N2 | 0.0548 (13) | 0.0442 (12) | 0.0365 (11) | −0.0219 (11) | 0.0201 (10) | −0.0207 (10) |
N3 | 0.0337 (10) | 0.0293 (10) | 0.0340 (9) | −0.0098 (8) | −0.0004 (8) | −0.0123 (8) |
N4 | 0.0540 (13) | 0.0300 (11) | 0.0570 (13) | −0.0038 (10) | −0.0074 (11) | −0.0217 (10) |
N5 | 0.0309 (9) | 0.0344 (10) | 0.0338 (9) | −0.0110 (8) | −0.0004 (8) | −0.0165 (8) |
N6 | 0.0446 (12) | 0.0496 (13) | 0.0551 (13) | −0.0161 (10) | −0.0082 (10) | −0.0302 (11) |
C1 | 0.0414 (13) | 0.0406 (13) | 0.0354 (12) | −0.0160 (11) | 0.0079 (10) | −0.0192 (11) |
C2 | 0.0655 (19) | 0.072 (2) | 0.0300 (13) | −0.0177 (16) | 0.0024 (13) | −0.0220 (14) |
C3 | 0.0421 (14) | 0.072 (2) | 0.0339 (12) | −0.0145 (14) | −0.0006 (11) | −0.0220 (13) |
C4 | 0.0624 (17) | 0.0394 (14) | 0.0413 (14) | −0.0205 (13) | 0.0099 (13) | −0.0139 (12) |
C5 | 0.085 (2) | 0.0319 (13) | 0.0465 (15) | −0.0187 (14) | −0.0014 (15) | −0.0077 (13) |
C6 | 0.0424 (13) | 0.0336 (12) | 0.0484 (14) | −0.0104 (10) | 0.0037 (11) | −0.0189 (11) |
C7 | 0.0393 (13) | 0.0368 (13) | 0.0503 (14) | −0.0081 (10) | −0.0105 (11) | −0.0196 (12) |
C8 | 0.0400 (13) | 0.0494 (15) | 0.0515 (15) | −0.0092 (11) | −0.0149 (12) | −0.0213 (13) |
C9 | 0.0397 (13) | 0.0366 (13) | 0.0534 (15) | −0.0090 (11) | −0.0095 (11) | −0.0211 (12) |
C10 | 0.0418 (12) | 0.0392 (12) | 0.0344 (12) | −0.0185 (10) | 0.0054 (10) | −0.0197 (11) |
C11 | 0.0545 (15) | 0.0434 (14) | 0.0258 (11) | −0.0190 (12) | −0.0067 (10) | −0.0102 (10) |
C12 | 0.0504 (14) | 0.0305 (11) | 0.0262 (10) | −0.0157 (10) | −0.0014 (10) | −0.0084 (9) |
C13 | 0.0343 (11) | 0.0274 (10) | 0.0236 (9) | −0.0098 (9) | 0.0024 (8) | −0.0112 (9) |
C14 | 0.0449 (13) | 0.0310 (11) | 0.0243 (10) | −0.0121 (10) | 0.0004 (9) | −0.0101 (9) |
C15 | 0.0501 (14) | 0.0319 (12) | 0.0293 (11) | −0.0184 (11) | 0.0034 (10) | −0.0098 (10) |
C16 | 0.0664 (19) | 0.068 (2) | 0.0525 (16) | −0.0307 (16) | −0.0052 (15) | −0.0326 (16) |
C17 | 0.0320 (10) | 0.0276 (10) | 0.0251 (10) | −0.0070 (8) | 0.0028 (8) | −0.0126 (9) |
Ni1—N3 | 2.127 (2) | C2—C3 | 1.358 (4) |
Ni1—N3i | 2.1266 (19) | C2—H2B | 0.9300 |
Ni1—N5 | 2.140 (2) | C3—H3A | 0.9300 |
Ni1—N5i | 2.1395 (18) | C4—C5 | 1.350 (4) |
Ni1—N1 | 2.141 (2) | C4—H4B | 0.9300 |
Ni1—N1i | 2.1406 (17) | C5—H5A | 0.9300 |
O1—C10 | 1.370 (3) | C6—H6B | 0.9300 |
O1—C16 | 1.422 (3) | C7—C8 | 1.357 (3) |
O2—C17 | 1.244 (2) | C7—H7A | 0.9300 |
O3—C17 | 1.266 (3) | C8—H8A | 0.9300 |
N1—C1 | 1.319 (3) | C9—H9A | 0.9300 |
N1—C3 | 1.372 (3) | C10—C11 | 1.385 (3) |
N2—C1 | 1.342 (3) | C10—C15 | 1.394 (3) |
N2—C2 | 1.347 (4) | C11—C12 | 1.392 (3) |
N2—H2A | 0.8600 | C11—H11A | 0.9300 |
N3—C6 | 1.310 (3) | C12—C13 | 1.384 (3) |
N3—C4 | 1.375 (3) | C12—H12A | 0.9300 |
N4—C6 | 1.342 (3) | C13—C14 | 1.395 (3) |
N4—C5 | 1.350 (4) | C13—C17 | 1.511 (3) |
N4—H4A | 0.8600 | C14—C15 | 1.382 (3) |
N5—C9 | 1.324 (3) | C14—H14A | 0.9300 |
N5—C7 | 1.370 (3) | C15—H15A | 0.9300 |
N6—C9 | 1.330 (3) | C16—H16A | 0.9600 |
N6—C8 | 1.362 (4) | C16—H16B | 0.9600 |
N6—H6A | 0.8600 | C16—H16C | 0.9600 |
C1—H1A | 0.9300 | ||
N3—Ni1—N3i | 180.00 (17) | C5—C4—H4B | 125.3 |
N3—Ni1—N5 | 90.40 (7) | N3—C4—H4B | 125.3 |
N3i—Ni1—N5 | 89.60 (7) | C4—C5—N4 | 106.8 (2) |
N3—Ni1—N5i | 89.60 (7) | C4—C5—H5A | 126.6 |
N3i—Ni1—N5i | 90.40 (7) | N4—C5—H5A | 126.6 |
N5—Ni1—N5i | 180.00 (11) | N3—C6—N4 | 112.0 (2) |
N3—Ni1—N1 | 89.75 (7) | N3—C6—H6B | 124.0 |
N3i—Ni1—N1 | 90.25 (7) | N4—C6—H6B | 124.0 |
N5—Ni1—N1 | 88.57 (7) | C8—C7—N5 | 109.8 (2) |
N5i—Ni1—N1 | 91.43 (7) | C8—C7—H7A | 125.1 |
N3—Ni1—N1i | 90.25 (7) | N5—C7—H7A | 125.1 |
N3i—Ni1—N1i | 89.75 (7) | C7—C8—N6 | 106.2 (2) |
N5—Ni1—N1i | 91.43 (7) | C7—C8—H8A | 126.9 |
N5i—Ni1—N1i | 88.57 (7) | N6—C8—H8A | 126.9 |
N1—Ni1—N1i | 180.00 (12) | N5—C9—N6 | 112.0 (2) |
C10—O1—C16 | 117.6 (2) | N5—C9—H9A | 124.0 |
C1—N1—C3 | 104.8 (2) | N6—C9—H9A | 124.0 |
C1—N1—Ni1 | 127.63 (17) | O1—C10—C11 | 124.8 (2) |
C3—N1—Ni1 | 127.57 (16) | O1—C10—C15 | 115.3 (2) |
C1—N2—C2 | 107.1 (2) | C11—C10—C15 | 119.9 (2) |
C1—N2—H2A | 126.5 | C10—C11—C12 | 119.6 (2) |
C2—N2—H2A | 126.5 | C10—C11—H11A | 120.2 |
C6—N3—C4 | 104.9 (2) | C12—C11—H11A | 120.2 |
C6—N3—Ni1 | 129.20 (16) | C13—C12—C11 | 121.1 (2) |
C4—N3—Ni1 | 125.88 (17) | C13—C12—H12A | 119.4 |
C6—N4—C5 | 106.8 (2) | C11—C12—H12A | 119.4 |
C6—N4—H4A | 126.6 | C12—C13—C14 | 118.6 (2) |
C5—N4—H4A | 126.6 | C12—C13—C17 | 120.85 (19) |
C9—N5—C7 | 104.8 (2) | C14—C13—C17 | 120.58 (19) |
C9—N5—Ni1 | 124.70 (17) | C15—C14—C13 | 121.0 (2) |
C7—N5—Ni1 | 129.16 (15) | C15—C14—H14A | 119.5 |
C9—N6—C8 | 107.2 (2) | C13—C14—H14A | 119.5 |
C9—N6—H6A | 126.4 | C14—C15—C10 | 119.8 (2) |
C8—N6—H6A | 126.4 | C14—C15—H15A | 120.1 |
N1—C1—N2 | 111.9 (2) | C10—C15—H15A | 120.1 |
N1—C1—H1A | 124.1 | O1—C16—H16A | 109.5 |
N2—C1—H1A | 124.1 | O1—C16—H16B | 109.5 |
N2—C2—C3 | 106.7 (2) | H16A—C16—H16B | 109.5 |
N2—C2—H2B | 126.6 | O1—C16—H16C | 109.5 |
C3—C2—H2B | 126.6 | H16A—C16—H16C | 109.5 |
C2—C3—N1 | 109.5 (2) | H16B—C16—H16C | 109.5 |
C2—C3—H3A | 125.2 | O2—C17—O3 | 123.7 (2) |
N1—C3—H3A | 125.2 | O2—C17—C13 | 119.01 (19) |
C5—C4—N3 | 109.5 (3) | O3—C17—C13 | 117.28 (18) |
N3—Ni1—N1—C1 | −97.2 (2) | N2—C2—C3—N1 | 0.4 (4) |
N3i—Ni1—N1—C1 | 82.8 (2) | C1—N1—C3—C2 | −0.3 (3) |
N5—Ni1—N1—C1 | 172.4 (2) | Ni1—N1—C3—C2 | −179.2 (2) |
N5i—Ni1—N1—C1 | −7.6 (2) | C6—N3—C4—C5 | 0.8 (3) |
N1i—Ni1—N1—C1 | −40 (100) | Ni1—N3—C4—C5 | −177.6 (2) |
N3—Ni1—N1—C3 | 81.5 (2) | N3—C4—C5—N4 | −0.7 (4) |
N3i—Ni1—N1—C3 | −98.5 (2) | C6—N4—C5—C4 | 0.3 (3) |
N5—Ni1—N1—C3 | −8.9 (2) | C4—N3—C6—N4 | −0.6 (3) |
N5i—Ni1—N1—C3 | 171.1 (2) | Ni1—N3—C6—N4 | 177.74 (16) |
N1i—Ni1—N1—C3 | 139 (100) | C5—N4—C6—N3 | 0.2 (3) |
N3i—Ni1—N3—C6 | −111 (100) | C9—N5—C7—C8 | 1.2 (3) |
N5—Ni1—N3—C6 | −67.2 (2) | Ni1—N5—C7—C8 | −165.85 (18) |
N5i—Ni1—N3—C6 | 112.8 (2) | N5—C7—C8—N6 | −1.3 (3) |
N1—Ni1—N3—C6 | −155.8 (2) | C9—N6—C8—C7 | 0.9 (3) |
N1i—Ni1—N3—C6 | 24.2 (2) | C7—N5—C9—N6 | −0.6 (3) |
N3i—Ni1—N3—C4 | 67 (100) | Ni1—N5—C9—N6 | 167.19 (16) |
N5—Ni1—N3—C4 | 110.9 (2) | C8—N6—C9—N5 | −0.2 (3) |
N5i—Ni1—N3—C4 | −69.1 (2) | C16—O1—C10—C11 | 2.1 (4) |
N1—Ni1—N3—C4 | 22.3 (2) | C16—O1—C10—C15 | −178.7 (2) |
N1i—Ni1—N3—C4 | −157.7 (2) | O1—C10—C11—C12 | 178.6 (2) |
N3—Ni1—N5—C9 | −168.7 (2) | C15—C10—C11—C12 | −0.6 (4) |
N3i—Ni1—N5—C9 | 11.3 (2) | C10—C11—C12—C13 | 0.8 (4) |
N5i—Ni1—N5—C9 | 96 (93) | C11—C12—C13—C14 | −0.4 (4) |
N1—Ni1—N5—C9 | −79.0 (2) | C11—C12—C13—C17 | 179.9 (2) |
N1i—Ni1—N5—C9 | 101.0 (2) | C12—C13—C14—C15 | −0.3 (4) |
N3—Ni1—N5—C7 | −4.0 (2) | C17—C13—C14—C15 | 179.4 (2) |
N3i—Ni1—N5—C7 | 176.0 (2) | C13—C14—C15—C10 | 0.6 (4) |
N5i—Ni1—N5—C7 | −100 (93) | O1—C10—C15—C14 | −179.4 (2) |
N1—Ni1—N5—C7 | 85.7 (2) | C11—C10—C15—C14 | −0.1 (4) |
N1i—Ni1—N5—C7 | −94.3 (2) | C12—C13—C17—O2 | 6.2 (3) |
C3—N1—C1—N2 | 0.0 (3) | C14—C13—C17—O2 | −173.6 (2) |
Ni1—N1—C1—N2 | 178.94 (16) | C12—C13—C17—O3 | −172.4 (2) |
C2—N2—C1—N1 | 0.2 (3) | C14—C13—C17—O3 | 7.8 (3) |
C1—N2—C2—C3 | −0.4 (3) |
Symmetry code: (i) −x+2, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.52 | 3.057 (4) | 121 |
N2—H2A···O2ii | 0.86 | 2.02 | 2.790 (3) | 147 |
N4—H4A···O3iii | 0.86 | 2.04 | 2.803 (3) | 147 |
N6—H6A···O2iv | 0.86 | 2.51 | 3.157 (3) | 132 |
N6—H6A···O3iv | 0.86 | 1.91 | 2.762 (3) | 169 |
C4—H4B···O1v | 0.93 | 2.56 | 3.307 (4) | 137 |
C9—H9A···N3i | 0.93 | 2.57 | 3.075 (4) | 114 |
C14—H14A···O3vi | 0.93 | 2.58 | 3.303 (3) | 134 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z+1; (iii) x+1, y−1, z; (iv) x+1, y, z; (v) x, y−1, z; (vi) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C3H4N2)6](C8H7O3)2 |
Mr | 769.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.8185 (4), 10.5191 (4), 10.8556 (5) |
α, β, γ (°) | 61.474 (1), 76.764 (1), 70.973 (1) |
V (Å3) | 927.62 (7) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.58 |
Crystal size (mm) | 0.50 × 0.24 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.759, 0.923 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6314, 4138, 3474 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.140, 1.00 |
No. of reflections | 4140 |
No. of parameters | 241 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −1.05 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
Ni1—N3 | 2.127 (2) | Ni1—N1 | 2.141 (2) |
Ni1—N5 | 2.140 (2) | ||
N3—Ni1—N5 | 90.40 (7) | N5—Ni1—N1 | 88.57 (7) |
N3—Ni1—N1 | 89.75 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.02 | 2.790 (3) | 147 |
N4—H4A···O3ii | 0.86 | 2.04 | 2.803 (3) | 147 |
N6—H6A···O3iii | 0.86 | 1.91 | 2.762 (3) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y−1, z; (iii) x+1, y, z. |
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Imidazole is of considerable interest as a potential binding site for metal ions in many biological systems. It is an unidentate ligand and forms complexes with metal ions through its tertiary nitrogen atom. Some complexes of imidazole and its derivatives with transition-metal ions have been reported (Brooks & Davidson, 1960; Davis & Smith, 1971). Complexes of copper(II) and cobalt(II) atoms with carboxylate and imidazole ligands have been studied as models for metalloproteins since both contain functionalities in the side chain (Sigel, 1980; Bernarducci et al., 1983; Abuhijleh & Woods, 1992). In addition, some of these copper(II) complexes were found to have a variety of pharmacological activities (Tamura et al., 1987) and superoxide dismutase activities (Bhirud & Srivastava, 1990). Complexes of [Co(RCOO)2(Im)2] (Im = –CH3, –C2H5) and model complexes for cobalt(II)-substituted zinc metalloenzymes, have been reported by Horrocks group (Horrocks et al., 1982).
The asymmetric unit of the title complex is formed by one-half of the hexakis(imidazole)nickel(II) molecule; the other half is related by inversion symmetry through the Ni atom located at the inversion centre and one methoxybenzoate molecule. The Ni atom is in an octahedral environment formed by the tertiary N atom of the imidazole moieties. The bond distances involved in this octahedral geometry, (Ni1—N1, Ni1—N2, Ni1—N3) ranging from 2.127 (2) Å to 2.141 (2) Å are comparable with those found in the complex of hexakis(imidazole)nickel(II) disalicylate (Jian et al., 1999). All the imidazole rings are planar. The methoxybenzoate moiety is planar with the maximum deviation of 0.111 (2) Å for the O3 atom.
In the solid state, intermolecular C—H.·O(x, y − 1, z) interactions connect the methoxybenzoate with the NiN6 chromophore. The complex forms a three-dimensional network through N—H···O intermolecular hydrogen bonds with the methoxybenzoate moieties acting as a bridge connecting the two hexakis(imidazole) nickel(II) molecules (figure 2). In addition, intra- and intermolecular C—H···π interactions contribute to the molecular packing (C3—H3A = 0.93; H3A···Cg1 = 2.77; C3···Cg1 = 3.481 Å; C3—H3···Cg1 = 134°, C16—H16C = 0.93; H16A···Cg2(1 − x, 1 − y, 1 − z) = 2.836; C16···Cg2 = 3.664 Å; C16—H16A···Cg2 = 145°, Cg1 = centroid of imidazole ring N5, N6, C7—C9 and Cg2 = centroid of C10—C15 ring).